Patent GB-403222-A (GB)
Title: Manufacture of azo-dyestuffs
IPC: C09B43/16
Filed: 1932-12-14
Abstract: Azo dyes of the type: <FORM:0403222/IV/1> in which one z = SO3H, one z = H, y and x = alkyl or alkoxy, R1 = the residue of ammonia or of a primary or secondary amine and R2 = the residue of a yellow aminoazo dyestuff are made by causing to react with each other in suitable sequence the diazotised dyestuff H acid (or O-acylesters) <FORM:0403222/IV/2> , H or K acid, cyanuric chloride, a yellow aminoazo dyestuff and ammonia or a compound containing a primary or secondary amino group, which compound is, when x and y = CH3 or when the yellow aminoazo dyestuff contains SO3H, any that may be selected, and in other cases is ammonia or a primary or secondary aliphatic amine or is a secondary aromatic amino compound containing an alkyl group in the amino group or an isocyclic mononuclear or poly-nuclear primary or secondary amino compound which contains at least 8 carbon atoms, and if desired, hydrolysing.  Dyestuffs fast to light and calcium carbonate are obtained.  In an example the following dyestuff is described: p-toluenesulphonic ester of H acid-->3-amino-4-cresolmethylether-->the ternary condensation product from cyanuric chloride, H acid, 4-amino-4<1>-oxyazobenzene-3<1>-carboxylic acid and monomethylaniline; the hydrolysed product dyes cotton and regenerated cellulose in green shades from a bath made with either soft or hard water.  In a table dyestuffs from the following additional components are specified: middle components:--1 : 4-dimethyl- or dimethoxy-2-aminobenzene, end components containing mono- and diethylamine, ammonia, monoethylaniline, 1 : 3 - dimethyl - 4 - aminobenzene or 1 : 4-dimethyl-2-aminobenzene, 1 - dimethylamino - 4 - aminobenzene, a  - or b -naphthylamine, 1 - naphthylamine - 6 - sulphonic acid, 2-naphthylamine-4 : 8-disulphonic acid, benzidine-2 : 2<1> disulphonic acid, aniline, 4 - amino - 3 - methoxyazobenzene - 3<1> - sulphonic acid, 2-naphthalene-4 : 8-disulpho acid - azo - 1 : 4 - dimethyl - 2 - aminobenzene and 2-naphthalene-8-sulpho acid-azo-1-methyl-3-amino-4-methoxybenzene as R1 in the above formula and 4 - amino - 3<1> - methyl - 4<1> - oxyazobenzene - 5<1> - carboxy acid, 4 - aminoazobenzene, 4 - amino - 3 - methoxyazobenzene - 3<1> - sulpho acid, 4 - amino - 4<1> - oxyazobenzene, 4 - amino - 2<1> - oxy - 5<1> - methylazobenzene, 4 - amino - 4<1> - oxy - 3<1> - or 2<1> - methylazobenzene, 4 - amino - 4<1> - oxy - 2<1> : 5<1> - methyl azobenzene, 4 - amino - 4<1> - oxyazobenzene - 3<1> - carboxylic acid as R2.  Specifications 209,723 and 326,791, [both in Class 2 (iii), Dyes &c.], are referred to.  The Specification as open to inspection under Sect. 91 comprises also dyestuffs of the above type in which K acid is the first component and in which the term R1 in the above formula may also be any mononuclear or polynuclear primary or secondary amino-compound which contains at least 8 carbon atoms. Dyestuffs may also be obtained from the diazotised dyestuff K acid (or an O- acyl ester) <FORM:0403222/IV/3> H or K acid, cyanuric chloride, a yellow aminoazo dyestuff, and ammonia or any amino compound.  An example is given of the following dyestuff: p-toluenesulphonic ester of K acid-->3 - amino - 4 - cresolmethylether--> ternary condensation product from cyanuric chloride, H acid, 4-amino-4<1>-oxyazobenzene-3<1>-carboxylic acid and aniline (hydrolysed).  In a table the following additional components are also specified (R1): sulphanilic acid, 4-chloraniline - 3 - sulphonic acid and 3 - aminobenzoic acid. This subject-matter does not appear in the Specification as accepted.